CA1321100C - Process for the preparation of an antioxydant extract of spices - Google Patents
Process for the preparation of an antioxydant extract of spicesInfo
- Publication number
- CA1321100C CA1321100C CA000576208A CA576208A CA1321100C CA 1321100 C CA1321100 C CA 1321100C CA 000576208 A CA000576208 A CA 000576208A CA 576208 A CA576208 A CA 576208A CA 1321100 C CA1321100 C CA 1321100C
- Authority
- CA
- Canada
- Prior art keywords
- extract
- process according
- polar solvent
- spice
- obtaining
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000284 extract Substances 0.000 title claims abstract description 57
- 235000013599 spices Nutrition 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 57
- 238000000605 extraction Methods 0.000 claims abstract description 33
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 28
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 27
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 18
- 239000002798 polar solvent Substances 0.000 claims abstract description 14
- 241001529742 Rosmarinus Species 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 235000002020 sage Nutrition 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 239000003759 ester based solvent Substances 0.000 claims 1
- 239000004210 ether based solvent Substances 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 230000009965 odorless effect Effects 0.000 abstract description 5
- 235000006708 antioxidants Nutrition 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229940092258 rosemary extract Drugs 0.000 description 8
- 235000020748 rosemary extract Nutrition 0.000 description 8
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 239000000469 ethanolic extract Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005325 percolation Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002027 dichloromethane extract Substances 0.000 description 2
- 239000002035 hexane extract Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002714 Extracts of rosemary Substances 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019306 extracts of rosemary Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/80—Freezing; Subsequent thawing; Cooling
- A23B2/803—Materials being transported through or in the apparatus, with or without shaping, e.g. in the form of powders, granules or flakes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/11—Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/46—Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polymers & Plastics (AREA)
- Botany (AREA)
- Epidemiology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Birds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3574/87A CH672048A5 (enrdf_load_stackoverflow) | 1987-09-16 | 1987-09-16 | |
| CH3574/87-8 | 1987-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1321100C true CA1321100C (en) | 1993-08-10 |
Family
ID=4258920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000576208A Expired - Lifetime CA1321100C (en) | 1987-09-16 | 1988-08-31 | Process for the preparation of an antioxydant extract of spices |
Country Status (21)
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5209870A (en) * | 1989-08-21 | 1993-05-11 | Kalamazoo Holdings, Inc. | Stable alkaline Labiatae antioxidant extracts |
| DK0507064T3 (da) * | 1991-03-30 | 1995-10-02 | Nestle Sa | Fremgangsmåde til opnåelse af en flydende antioxidantekstrakt fra krydderier |
| US5145955A (en) * | 1991-10-28 | 1992-09-08 | Council Of Scientific & Industrial Research | Process for the preparation and composition of a fraction containing picroside I and kutkoside |
| DE4207739A1 (de) * | 1992-03-11 | 1993-09-16 | Sueddeutsche Kalkstickstoff | Verfahren zur herstellung von natuerlichen antioxidantien |
| FR2695034B1 (fr) | 1992-09-01 | 1994-10-07 | Oreal | Composition cosmétique ou pharmaceutique comprenant en association une peroxydase et un agent anti-oxygène singulet. |
| FR2697159B1 (fr) * | 1992-10-22 | 1995-01-13 | Oreal | Composition cosmétique ou dermo-pharmaceutique contenant en association un lauroylméthionate d'un amino acide basique et au moins un polyphénol. |
| FR2699818B1 (fr) * | 1992-12-24 | 1995-02-03 | Oreal | Composition cosmétique ou pharmaceutique contenant en association un polyphénol et un extrait de gingko. |
| US5585130A (en) * | 1993-08-17 | 1996-12-17 | Nestec S.A. | Concentration of antioxidants in fats |
| ATE163838T1 (de) * | 1993-08-17 | 1998-03-15 | Nestle Sa | Verfahren zum extrahieren von pflanzlicher antioxidanten in flüssiger form |
| DK0658316T3 (da) * | 1993-12-17 | 1999-11-15 | Nestle Sa | Fremgangsmåde til beskyttelse af et fedtstof mod oxidation |
| US6051256A (en) * | 1994-03-07 | 2000-04-18 | Inhale Therapeutic Systems | Dispersible macromolecule compositions and methods for their preparation and use |
| US5773075A (en) * | 1996-12-13 | 1998-06-30 | Kalamazoo Holdings, Inc. | High temperature countercurrent solvent extraction of Capsicum solids |
| US20030203036A1 (en) * | 2000-03-17 | 2003-10-30 | Gordon Marc S. | Systems and processes for spray drying hydrophobic drugs with hydrophilic excipients |
| AU5806998A (en) * | 1996-12-31 | 1998-07-31 | Inhale Therapeutic Systems | Processes for spray drying solutions of hydrophobic drugs with hydrophilic excipients and compositions prepared by such processes |
| US5985345A (en) * | 1997-12-12 | 1999-11-16 | Kalamazoo Holdings, Inc. | High temperature extraction of spices and herbs |
| FR2772561B1 (fr) * | 1997-12-24 | 2000-12-29 | Aromes Et Parfums Franc | Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette |
| SI20143B (sl) * | 1999-02-16 | 2008-04-30 | Vitiva Prizvodnja In Storitve D.D. | Postopek za pridobivanje naravnih antioksidantov iz rastlin |
| US7575761B2 (en) * | 2000-06-30 | 2009-08-18 | Novartis Pharma Ag | Spray drying process control of drying kinetics |
| WO2002009669A2 (en) * | 2000-08-01 | 2002-02-07 | Inhale Therapeutic Systems, Inc. | Apparatus and process to produce particles having a narrow size distribution and particles made thereby |
| WO2003037303A1 (en) | 2001-11-01 | 2003-05-08 | Nektar Therapeutics | Spray drying methods and compositions thereof |
| GB0216562D0 (en) * | 2002-04-25 | 2002-08-28 | Bradford Particle Design Ltd | Particulate materials |
| US9339459B2 (en) | 2003-04-24 | 2016-05-17 | Nektar Therapeutics | Particulate materials |
| MXPA05007154A (es) * | 2002-12-30 | 2005-09-21 | Nektar Therapeutics | Atomizador prepeliculizacion. |
| AU2004220556B2 (en) | 2003-03-07 | 2009-05-07 | Alnylam Pharmaceuticals, Inc. | Therapeutic compositions |
| ES2702942T3 (es) | 2003-04-17 | 2019-03-06 | Alnylam Pharmaceuticals Inc | Agentes de ARNi modificados |
| US20050175717A1 (en) * | 2004-01-29 | 2005-08-11 | L'oreal | (Cosmetic) composition, process of making, uses thereof |
| CA2633571A1 (en) * | 2005-12-16 | 2007-07-05 | Bakto Natural Preservatives, Llc | Recovery of residual plant components after distillation of essential oils |
| CA3043911A1 (en) | 2007-12-04 | 2009-07-02 | Arbutus Biopharma Corporation | Targeting lipids |
| CA3044980A1 (en) | 2008-04-11 | 2009-10-15 | Alnylam Pharmaceuticals, Inc. | Site-specific delivery of nucleic acids by combining targeting ligands with endosomolytic components |
| WO2011109427A2 (en) | 2010-03-01 | 2011-09-09 | Alnylam Pharmaceuticals, Inc. | Improving the biological activity of sirna through modulation of its thermodynamic profile |
| WO2016020339A2 (en) * | 2014-08-05 | 2016-02-11 | Cutech Srl | Extracts of microalgae and plants for regulating sebum production |
| WO2016057693A1 (en) | 2014-10-10 | 2016-04-14 | Alnylam Pharmaceuticals, Inc. | Methods and compositions for inhalation delivery of conjugated oligonucleotide |
| JP7039142B2 (ja) * | 2019-04-05 | 2022-03-22 | 長谷川香料株式会社 | 飲食品の風味付与ないし増強剤 |
| FR3132022A1 (fr) | 2022-01-25 | 2023-07-28 | L'oreal | Utilisation de polyphénol et de polymère soluble dans l’eau pour le traitement de fibres kératiniques |
| FR3132020A1 (fr) | 2022-01-21 | 2023-07-28 | L'oreal | Utilisation de polyphénol et de protéine dérivée de plantes pour le traitement de fibres kératiniques |
| WO2023112869A1 (en) | 2021-12-17 | 2023-06-22 | L'oreal | Use of polyphenol and water-soluble polymer for treating keratin fibers |
| WO2023112868A1 (en) | 2021-12-17 | 2023-06-22 | L'oreal | Use of polyphenol and protein derived from plants for treating keratin fibers |
| FR3131837B1 (fr) | 2022-01-19 | 2024-10-04 | Oreal | Composition stable comprenant un rétinoïde et un composé acide ascorbique |
| EP4452190A1 (en) | 2021-12-20 | 2024-10-30 | L'oreal | Stable composition comprising retinoid and ascorbic acid compound |
| WO2023120259A1 (en) | 2021-12-20 | 2023-06-29 | Oreal | Stable composition comprising retinoid |
| FR3131845B1 (fr) | 2022-01-19 | 2024-11-01 | Oreal | Composition stable comprenant un rétinoïde |
| WO2024135577A1 (en) | 2022-12-23 | 2024-06-27 | L'oreal | Stable dispersion composition comprising retinoid |
| FR3145278A1 (fr) | 2023-01-30 | 2024-08-02 | L'oreal | Composition de dispersion stable comprenant un rétinoïde |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1419958A (en) * | 1972-07-19 | 1975-12-31 | Brooke Bond Liebig Ltd | Extraction of flavour and fragrance components from plant material |
| CH579354A5 (enrdf_load_stackoverflow) * | 1973-10-26 | 1976-09-15 | Nestle Sa | |
| US3950266A (en) * | 1973-11-28 | 1976-04-13 | Rutgers Research And Educational Foundation | Method of producing an antioxidant composition from rosemary and sage |
| US3950226A (en) * | 1974-10-31 | 1976-04-13 | Moon Ki Chang | Novel reagent and method for the determination of urea in biological fluids |
| CH634726A5 (fr) * | 1978-09-29 | 1983-02-28 | Nestle Sa | Procede de preparation de substances antioxygenes. |
| JPS55102508A (en) * | 1979-02-01 | 1980-08-05 | Lion Corp | Preparation of antiseptic |
| JPS56144078A (en) * | 1980-04-08 | 1981-11-10 | Lion Corp | Preparation of preservative |
| US4450097A (en) * | 1981-02-26 | 1984-05-22 | Lion Corporation | Antioxidative compound, method of extracting same from rosemary, and use of same |
| CA1297718C (en) * | 1985-12-20 | 1992-03-24 | Paul H. Todd, Jr. | Herb flavoring and/or antioxidant composition and process |
-
1987
- 1987-09-16 CH CH3574/87A patent/CH672048A5/fr not_active IP Right Cessation
-
1988
- 1988-08-13 DE DE8888113185T patent/DE3870777D1/de not_active Expired - Lifetime
- 1988-08-13 AT AT88113185T patent/ATE75585T1/de not_active IP Right Cessation
- 1988-08-13 ES ES198888113185T patent/ES2031190T3/es not_active Expired - Lifetime
- 1988-08-13 EP EP88113185A patent/EP0307626B1/fr not_active Expired - Lifetime
- 1988-08-23 IE IE256888A patent/IE61538B1/en not_active IP Right Cessation
- 1988-08-23 AU AU21488/88A patent/AU612687B2/en not_active Ceased
- 1988-08-25 ZA ZA886341A patent/ZA886341B/xx unknown
- 1988-08-25 US US07/236,504 patent/US5026550A/en not_active Expired - Lifetime
- 1988-08-31 CA CA000576208A patent/CA1321100C/en not_active Expired - Lifetime
- 1988-09-06 NO NO883964A patent/NO172163C/no not_active IP Right Cessation
- 1988-09-10 MY MYPI88001012A patent/MY103911A/en unknown
- 1988-09-14 EG EG481/88A patent/EG18308A/xx active
- 1988-09-14 OA OA59430A patent/OA08914A/xx unknown
- 1988-09-14 NZ NZ226188A patent/NZ226188A/xx unknown
- 1988-09-14 JP JP63231408A patent/JPH0657118B2/ja not_active Expired - Fee Related
- 1988-09-14 MX MX013027A patent/MX169362B/es unknown
- 1988-09-15 AR AR88311947A patent/AR241850A1/es active
- 1988-09-15 PT PT88517A patent/PT88517B/pt not_active IP Right Cessation
-
1992
- 1992-05-08 GR GR920400887T patent/GR3004542T3/el unknown
- 1992-11-06 SG SG1182/92A patent/SG118292G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE882568L (en) | 1989-03-16 |
| EG18308A (en) | 1992-10-30 |
| NO172163B (no) | 1993-03-08 |
| MY103911A (en) | 1993-10-30 |
| IE61538B1 (en) | 1994-11-16 |
| PT88517B (pt) | 1992-11-30 |
| EP0307626A1 (fr) | 1989-03-22 |
| NO883964L (no) | 1989-03-17 |
| MX169362B (es) | 1993-06-30 |
| NO172163C (no) | 1993-06-16 |
| ES2031190T3 (es) | 1992-12-01 |
| NO883964D0 (no) | 1988-09-06 |
| GR3004542T3 (enrdf_load_stackoverflow) | 1993-04-28 |
| JPH0657118B2 (ja) | 1994-08-03 |
| EP0307626B1 (fr) | 1992-05-06 |
| AU2148888A (en) | 1989-03-16 |
| AU612687B2 (en) | 1991-07-18 |
| ATE75585T1 (de) | 1992-05-15 |
| SG118292G (en) | 1993-01-29 |
| DE3870777D1 (de) | 1992-06-11 |
| CH672048A5 (enrdf_load_stackoverflow) | 1989-10-31 |
| JPH01108952A (ja) | 1989-04-26 |
| PT88517A (pt) | 1988-10-01 |
| NZ226188A (en) | 1991-01-29 |
| OA08914A (fr) | 1989-10-31 |
| US5026550A (en) | 1991-06-25 |
| ZA886341B (en) | 1989-04-26 |
| AR241850A1 (es) | 1993-01-29 |
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| HK1187016B (en) | Simple process to produce and separate water soluble and oil soluble antioxidative flavoring compositions from labiatae herbs using green solvents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed | ||
| MKEC | Expiry (correction) |
Effective date: 20121205 |